ArticleNature communications2021
Enantioselective synthesis of tertiary boronic esters through catalytic asymmetric reversed hydroboration.
Article in Nature communications, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 31 citations in OpenAlex.
- Catalytic Stereospecific Construction of Aminocyclopropanes from β-Boryl Amides.Journal of the American Chemical Society · 2026Article
- The current utility and future potential of multiborylated alkanes.Nature reviews. Chemistry · 2024Review
- Nanocomposites of Poly(Polymers · 2024Article
- Copper-catalyzed carbonylative multi-component borylamidation of alkenes for synthesizing γ-boryl amides with CO as both methylene and carbonyl sources.Chemical science · 2024Article
- Copper-Metallized Porous N-Heterocyclic Carbene Ligand Polymer-Catalyzed Regio- and Stereoselective 1,2-Carboboration of Alkynes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Bifunctional Iminophosphorane-Catalyzed Enantioselective Sulfa-Michael Addition to Unactivated α,β-Unsaturated Amides.Journal of the American Chemical Society · 2022Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Chiral tertiary boronic esters are important precursors to bioactive compounds and versatile synthetic intermediates to molecules containing quaternary stereocenters. The development of conjugate boryl addition to α,β-unsaturated amide has been hampered by the intrinsic low electrophilicity of the amide group. Here we show the catalytic asymmetric synthesis of enantioenriched tertiary boronic esters through hydroboration of β,β-disubstituted α,β-unsaturated amides. The Rh-catalyzed hydroboration occurs with previously unattainable selectivity to provide tertiary boronic esters in high enantioselectivity. This strategy opens a door for the hydroboration of inert Michael acceptors with high stereocontrol and may provide future applications in the synthesis of biologically active molecules.
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Registered trials
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